Substituted 2-phenylpyridines as herbicides

ABSTRACT

2-Phenylpyridines I                    
     an their salts, 
     wherein R 1  to R 17 , X 1 -X 3  are as defined in the specification. The compounds are useful as herbicides, desiccants and defoliants.

This application is a 371 of PCT/EP00/00095 filed Jan. 8, 2000 now WO00/42015 filed Jul. 20, 2000.

The present invention relates to novel substituted 2-phenyl-5 pyridinesof the formula I

where:

n is zero or 1;

R¹ is aminosulfonyl, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl orC₁-C₆-haloalkylsulfonyl;

R²,R³ independently of one another are hydrogen or halogen;

R⁴ is cyano, hydroxyl, halogen, C₁-C₆-alkoxy or phenylmethoxy, where thephenyl ring may be unsubstituted or may carry from one to threesubstituents, in each case selected from the group consisting ofhydroxyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, hydroxycarbonyl, (C₁-C₆-alkoxy)carbonyl and(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy;

R⁵ is hydrogen, nitro, cyano, hydroxylamino, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, —COCl, —CO—OR⁶, —CO—N(R⁷)R⁸,—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CO—O—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸,—X¹—(C₁-C₄-alkylene)—CO—OR⁶, —X¹—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸, —X¹—R⁹, —CH═C(R¹⁰)—CO—OR⁶,—CH═C(R¹⁰)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CH═C(R¹⁰)—CO—N(R⁷)R⁸, formyl,—CO—R⁶,

 —C(R⁸)═N—OR¹⁵, —X¹—(C₁-C₄-alkylene)—C(R⁸)═N—OR¹⁵,—CH═C(R¹⁰)—C(R⁸)═N—OR¹⁵, —CH(C₁-C₆-alkoxy)₂, —CN(R¹⁶)R¹⁷,—N(R¹⁶)—SO₂—(C₁-C₆-alkyl), —N(R¹⁶)—CO—(C₁-C₆-alkyl), chlorosulfonyl,hydroxysulfonyl or —SO₂—N(R¹⁸)R¹⁹;

R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₃-C₆-cycloalkyl or C₁-C₆-alkoxy-C₁-C₆-alkyl;

R⁷ is hydrogen or C₁-C₆-alkyl;

R⁸ is hydrogen, hydroxyl, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,phenyl-C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or C₃-C₆-alkynyloxy;

R⁹ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₃-C₆-cycloalkyl or C₁-C₆-alkoxy-C₁-C₆-alkyl;

R¹⁰ is hydrogen, halogen or C₁-C₆-alkyl;

R¹¹-R¹⁴ independently of one another are hydrogen, C₁-C₆-alkyl or(C₁-C₆-alkoxy)carbonyl;

R¹⁵ is hydrogen, C₁-C₆-alkyl, phenyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹⁶ is hydrogen or C₁-C₆-alkyl;

R¹⁷ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy;

R¹⁸ is hydrogen or C₁-C₆-alkyl;

R¹⁹ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy;

X¹-X³ independently of one another are oxygen or sulfur;

and the agriculturally useful salts of the compounds I whereR⁶=hydrogen.

Moreover, the invention relates to

the use of the compounds I as herbicides or for thedesiccation/defoliation of plants,

herbicidal compositions and compositions for the desiccation and/ordefoliation of plants which comprise the compounds I as activeingredients,

methods for controlling undesirable vegetation and for the desiccationand/or defoliation of plants using the compounds I,

processes for preparing the compounds I and herbicidal compositions andcompositions for the desiccation and/or defoliation of plants using thecompounds I and also

intermediates of the formula IIa.

WO 96/21646 and WO 96/21647 have already described certain substituted2-phenylpyridines of the type of the compounds I having, inter alia,C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl in the 5-position of thepyridine ring for use as herbicides and desiccants/defoliants.

Furthermore, 2-phenylpyridines having herbicidal and/ordesiccant/defoliant activity, which differ from the present compounds Iin that R¹ is directly attached to the pyridine ring, form part of thesubject matter of WO 98/07700.

However, the herbicidal activity of the prior art compounds is, with aview to the harmful plants, not always entirely satisfactory.

It is an object of the present invention, therefore, to provide novelherbicidally active compounds which allow better selective control ofundesirable plants than known compounds. It is a further object toprovide novel compounds which have a desiccant/defoliant action.

We have found that these objects are achieved by the herbicidalsubstituted 2-phenylpyridines of the formula I defined at the outset andby novel intermediates IIa for their preparation.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal activity. Moreover, we havefound processes for preparing these compositions and methods forcontrolling undesirable vegetation using the compounds I.

Furthermore, we have found that the compounds I are also suitable forthe desiccation/defoliation of parts of plants, suitable plants beingcrop plants such as cotton, potatoes, oilseed rape, sunflower, soybeanor field beans, in particular cotton and potatoes. In this regard, wehave found compositions for the desiccation and/or defoliation ofplants, processes for preparing these compositions and methods for thedesiccation and/or defoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they exist in theform of enantiomer or diastereomer mixtures. The invention provides boththe pure enantiomers or diastereomers and mixtures thereof.

The substituted 2-phenylpyridines I where R⁶=hydrogen may be present inthe form of their agriculturally useful salt, the type of salt beinggenerally immaterial. In general, the salts of such bases are suitablewhere the herbicidal activity is not adversely affected in comparison tothe free compound I.

Suitable salts are, in particular, those of the alkali metals,preferably sodium and potassium salts, the alkaline earth metals,preferably calcium and magnesium salts, those of the transition metals,preferably zinc and iron salts, and also ammonium salts, where theammonium ion may, if desired, carry one to four C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl substituents and/or one phenyl or benzylsubstituent, preferably diisopropylammonium, tetramethylammonium,tetrabutylammonium, trimethylbenzylammonium andtrimethyl-(2-hydroxyethyl)ammonium salts, furthermore phosphonium salts,sulfonium salts, such as, preferably, tri-(C₁-C₄-alkyl)sulfonium salts,and sulfoxonium salts, such as, preferably, tri-(C₁-C₄-alkyl)sulfoxoniumsalts.

The organic molecular moieties mentioned for the substituents R¹ and R⁴to R¹⁹ or as radicals on a phenyl ring are collective terms forindividual listings of the individual group members. All hydrocarbonchains, i.e. all alkyl, haloalkyl, phenylalkyl, alkylene, alkoxy,haloalkoxy, phenylalkoxy, alkylsulfinyl, alkylsulfonyl,hydroxycarbonylalkyl, alkenyl, alkynyl, alkenyloxy and alkynyloxymoieties can be straight-chain or branched. Halogenated substituentspreferably carry one to five identical or different halogen atoms.

The term halogen represents in each case fluorine, chlorine, bromine oriodine, in particular fluorine or chlorine.

Examples of other meanings are:

C₁-C₆-alkyl: C₁-C₄-alkyl such as CH₃, C₂H₅, CH₂-C₂H₅, CH(CH₃)₂, n-butyl,CH(CH₃)—C₂H₅, CH₂—CH(CH₃)₂ and C(CH₃)₃, or, for example, n-pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethyipropyl,1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylp ropyl,1-methylpentyl , 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH₃,C₂H₅, CH₂—C₂H₅, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₆-haloalkyl: a C₁-C₆-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, CH₂F, CHF₂, CF₃, CH₂Cl, CH(Cl)₂, C(Cl)₃,CHFCl, CF(Cl)₂, CF₂Cl, CF₂Br, 1-fluoroethyl, 2-fluoroethyl,2-chloroethyl , 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,1,2-dichloroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluoropropyl,3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl,3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl,3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH₂—C₂F₅, CF₂—C₂F₅,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl,4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl,5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undecafluoropentyl,6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl,6,6,6-trichlorohexyl or dodecafluorohexyl, in particular CH₂F, CHF₂,CF₃, CH₂C_(1,2)-fluoroethyl, 2-chloroethyl, 1,2-dichloroethyl,2,2,2-trifluoroethyl or C₂F₅;

Phenyl-C₁-C₆-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl,1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl,1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl,1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl, 1-(benzyl)prop-1-ylor 2-phenylhex-6-yl, in particular benzyl or 2-phenylethyl;

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, inparticular cyclopentyl or cyclohexyl;

C₁-C₄-alkylene: —CH₂—, —CH(CH₃)—, 1,2-ethylene, 1,1-propylene,1,2-propylene, 1,3-propylene, —CC(CH₃)₂—, 1,1-butylene, 1,2-butylene,1,3-butylene, 1,4-butylene, 2,2-butylene, 2,3-butylene,2-methyl-1,1-propylene, 2-methyl-1,2-propylene or2-methyl-1,3-propylene, preferably methylene, 1,1-ethylene,1,2-ethylene, 1,1-propylene or 2,2-propylene;

C₁-C₆-alkoxy: for example OCH₃, OC₂H₅, n-propoxy, OCH(CH₃)₂, n-butoxy,OCH(CH₃)—C₂H₅, OCH₂-CH(CH₃)₂, OC(CH₃)₃, n-pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy, in particular OCH₃, OC₂H₅, OCH(CH₃)₂ orOC(CH₃)₃;

C₁-C₆-haloalkoxy: C₁-C₆-alkoxy as mentioned above which is partially orfully substituted by fluorine, chlorine, bromine and/or iodine, i.e.,for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, OCHFC₁,OCF(Cl)₂, OCF₂Cl, OCF₂Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy,3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, OCF₂—C₂F₅,1—(CH₂F)-2-fluoroethoxy, 1—(CH₂Cl)-2-chloroethoxy,1—(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy,nonafluorobutoxy, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlbrohexoxy,6-bromohexoxy or dodecafluorohexoxy;

Phenyl-C₁-C₆-alkoxy: for example benzyloxy, 1-phenylethoxy,2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy,3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy,3-phenylbut-1-yloxy, 4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy,2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy,1-(benzyl)eth-1-yloxy, 1-(benzyl)₁-(methyl)eth-1-yloxy,1-(benzyl)prop-1-yloxy or 2-phenylhex-6-yloxy, in particular benzyloxyor 2-phenylethoxy;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted byC₁-C₆-alkoxy as mentioned above, i.e., for example, CH₂OCH₃, CH₂OC₂H₅,CH₂OCH₂—C₂H₅, CH₂OCH(CH₃)₂, CH₂OCH₂CH₅, (1-methylpropoxy)methyl,(2-methylpropoxy)methyl, CH₂OC(CH₃)₃, CH₂O(CH₂)₃—C₂H₅, CH₂O(CH₂)₄—C₂H₅,CH(CH₃)OCH₃, CH(CH₃)OC₂H₅, CH₂CH₂OCH₃, CH₂CH₂OC₂H₅, CH₂CH₂OCH₂—C₂H₅,CH₂CH₂OH(CH₃)₂, CH₂CH₂OCH₂CH₂—C₂H₅, 2-(1-methylpropoxy)ethyl,2-(2-methylpropoxy)ethyl, CH₂CH₂OC(CH₃)₃, CH₂CH₂O(CH₂)₃—C₂H₅,CH₂CH₂O(CH₂)₄—C₂H₅, 2-(OCH₃)propyl, 2-(OC₂H₅)propyl,2-(OCH₂—C₂H₅)propyl, 2-[OCH(CH₃)₂]propyl, 2-(OCH₂CH₂—C₂H₅)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-[OC(CH₃)₃]propyl, 3-(OCH₃)propyl, 3-(OC₂H₅)propyl,3-(OCH₂—C₂H₅)propyl, 3-[OCH(CH₃)₂]propyl, 3-(OCH₂CH₂—C₂H₅)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-[OC(CH₃)₃]propyl, 3-[O(CH₂)₃—C₂H₅]propyl, 3-[O(CH₂)₄—C₂H₅]propyl,2-(OCH₃)butyl, 2-(OC₂H₅)butyl, 2-(OCH₂—C₂H₅)butyl, 2-[OCH(CH₃)₂]butyl,2-(OCH₂CH₂—C₂H₅)butyl, 2-(1-methylpropoxy)butyl,2-(2-methylpropoxy)butyl, 2-[OC(CH₃)₃]butyl, 3-(OCH₃)butyl,3-(OC₂H₅)butyl, 3-(OCH₂—C₂H₅)butyl, 3-[OCH(CH₃)₂]butyl,3-(OCH₂CH₂—C₂H₅)butyl, 3-(1-methylpropoxy)butyl,3-(2-methylpropoxy)butyl, 3-[OC(CH₃)₃]butyl, 4-(OCH₃)butyl,4-(OC₂H₅)butyl, 4-(OCH₂—C₂H₅)butyl, 4-[OCH(CH₃)₂]butyl,4-(OCH₂CH₂—C₂H₅)butyl, 4-(1-methylpropoxy)butyl,4-(2-methylpropoxy)butyl, 4-[OC(CH₃)₃]butyl, 4-[O(CH₂)₃—C₂H₅]butyl,4-[O(CH₂)₄—C₂H₅]butyl, 5-(OCH₃)pentyl, 5-(OC₂H₅)pentyl,5-(OCH₂—C₂H₅)pentyl, 5-[OCH(CH₃)₂]pentyl, 5-(OCH₂CH₂—C₂H₅)pentyl,5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl,5-[OC(CH₃)₃]pentyl, 5-[O(CH₂)₃—C₂H₅]pentyl, 5-[O(CH₂)₄—C₂H₅]pentyl,6-(OCH₃)hexyl, 6-(OC₂H₅)hexyl, 6-(OCH₂—C₂H₅)hexyl, 6-[OCH(CH₃)₂]hexyl,6-(OCH₂CH₂—C₂H₅)hexyl, 6-(1-Methylpropoxy)hexyl,6-(2-methylpropoxy)hexyl, 6-[OC(CH₃)₃]hexyl, 6-[O(CH₂)₃—C₂H₅]hexyl or6-[O(CH₂)₄—C₂H₅]hexyl, in particular CH₂OCH₃, CH(CH₃)OCH₃, CH₃CH₂OCH₃ orCH(CH₃)CH₂OCH₃;

Hydroxycarbonyl-C₁-C₆-alkyl: for example CH₂COOH, CH(CH₃)COOH,CH₂CH₂COOH, 1-(COOH)prop-1-yl, 2-(COOH)prop-1-yl, 3-(COOH)prop-1-yl,1-(COOH)but-1-yl, 2-(COOH)but-1-yl, 3-(COOH)but-1-yl, 4-(COOH)but-1-yl,1-(COOH)but-2-yl, 2-(COOH)but-2-yl, 3-(COOH)but-2-yl, 4-(COOH)but-2-yl,1-(CH₂COOH)eth-1-yl, 1-(CH₂COOH)-1-(CH₃)eth-1-yl, 1-(CH₂COOH)prop-1-yl,5-(COOH)pent-1-yl or 6-(COOH)hex-1-yl;

(C₁-C₆-alkoxy)carbonyl: COOCH₃, COOC₂H₅, n-propoxycarbonyl, OCH(CH₃)₂,n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl,OC(CH₃)₃, n-pentoxycarbonyl, 1-methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl,1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,1-C₂H₅-1-CH₃-propoxycarbonyl or 1-C₂H₅-2-CH₃-propoxycarbonyl, inparticular COOCH₃, COOC₂H₅ or COOC(CH₃)₃;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by(C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example, CH₂COOCH₃,CH₂COOC₂H₅, CH₂COOCH₂—C₂H₅, CH₂COOCH(CH₃)₂, CH₂COOCH₂CH₂—C₂H₅,(1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl,CH₂COOC(CH₃)₃, CH₂COO(CH₂)₃—C₂H₅, CH₂COO(CH₂)₄—C₂H₅, CH(CH₃)COOCH₃,CH(CH₃)COOC₂H₅, CH₂CH₂COOCH₃, CH₂CH₂COOC₂H₅, CH₂CH₂COOCH₂—C₂H₅,CH₂CH₂COOCH(CH₃)₂, CH₂CH₂COOCH₂CH₂—C₂H₅,2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)ethyl,CH₂CH₂COOC(CH₃)₃, CH₂CH₂COO(CH₂)₃—C₂H₅, CH₂CH₂COO(CH₂)₄—C₂H₅,2-(COOCH₃)propyl, 2-(COOC₂H₅)propyl, 2-(COOCH₂—C₂H₅)propyl,2-[COOCH(CH₃)₂]propyl, 2-(COOCH₂CH₂—C₂H₅)propyl,2-(1-methylpropoxycarbonyl)propyl, 2-(2-methylpropoxycarbonyl)propyl,2-[COOC(CH₃)₃]propyl, 3-(COOCH₃)propyl, 3-(COOC₂H₅)propyl,3-(COOCH₂—C₂H₅)propyl, 3-[COOCH(CH₃)₂]propyl, 3-(COOCH₂CH₂—C₂H₅)propyl,3-(1-methylpropoxycarbonyl)propyl, 3-(2-methylpropoxycarbonyl)propyl,3-[COOC(CH₃)₃]propyl, 3-[COO(CH₂)₃—C₂H₅]propyl,3-[COO(CH₂)₄—C₂H₅]propyl, 2-(COOCH₃)butyl, 2-(COOC₂H₅)butyl,2-(COOCH₂—C₂H₅)butyl, 2-[COOCH(CH₃)₂]butyl, 2-(COOCH₂CH₂—C₂H₅)butyl,2-(l-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)butyl,2-[COOC(CH₃)₃]butyl, 3-(COOCH₃)butyl, 3-(COOC₂H₅)butyl,3-(COOCH₂—C₂H₅)butyl, 3-[COOCH(CH₃)₂]butyl, 3-(COOCH₂CH₂—C₂H₅)butyl,3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl,3-[COOC(CH₃)₃]butyl, 4-(COOCH₃)butyl, 4-(COOC₂H₅)butyl,4-(COOCH₂—C₂H₅)butyl, 4-[COOCH(CH₃)₂]butyl, 4-(COOCH₂CH₂—C₂H₅)butyl,4-(1-methylpropoxycarbonyl)butyl, 4-(2-methylpropoxycarbonyl)butyl,4-[COOC(CH₃)₃]butyl, 4-[COO(CH₂)₃-C₂H₅]butyl, 4-[COO(CH₂)₄—C₂H₅]butyl,5-(COOCH₃)pentyl, 5-(COOC₂H₅)pentyl, 5-(COOCH₂—C₂H₅)pentyl,5-[COOCH(CH₃)₂]pentyl, 5-(COOCH₂CH₂—C₂H₅)pentyl,5-(1-methylpropoxycarbonyl)pentyl, 5-(2-methylpropoxycarbonyl)pentyl,5-[COOC(CH₃)₃]pentyl, 5-[COO(CH₂)₃—C₂H₅]pentyl,5-[COO(CH₂)₄—C₂H₅]pentyl, 6-(COOCH₃)hexyl, 6-(COOC₂H₅)hexyl,6-(COOCH₂—C₂H₅)hexyl, 6-[COOCH(CH₃)₂]hexyl, 6-(COOCH₂CH₂—C₂H₅)hexyl,6-(1-methylpropoxycarbonyl)hexyl, 6-(2-methylpropoxycarbonyl)hexyl,6-[COOC(CH₃)₃]hexyl, 6-[COO(CH₂)₃—C₂H₅]hexyl or 6-[COO(CH₂)₄—C₂H₅]hexyl,in particular CH₂COOCH₃, CH₂COOCH(CH₃)₂ or CH(CH₃)COOCH₃;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy: C₁-C₆-alkoxy which is substitutedby (C₁-C₆-alkoxy)carbonyl as mentioned above, i.e., for example,OCH₂COOCH₃, OCH₂COOC₂H₅, OCH₂COOCH₂—C₂H₅, OCH₂COOCH(CH₃)₂,OCH₂COOCH₂CH₂—C₂H₅, (1-methylpropoxycarbonyl)-methoxy,(2-methylpropoxycarbonyl)methoxy, OCH₂COOC(CH₃)₃, OCH₂COO(CH₂)₃—C₂H₅,OCH₂COO(CH₂)₄—C₂H₅, OCH(CH₃)COOCH₃, OCH(CH₃)COOC₂H₅, OCH₂CH₂COOCH₃,OCH₂CH₂COOC₂H₅, OCH₂CH₂COOCH₂—C₂H₅, OCH₂CH₂COOCH(CH₃)₂,OCH₂CH₂COOCH₂CH₂—C₂H₅, 2-(1-methylpropoxycarbonyl)ethoxy,2-(2-methylpropoxycarbonyl)ethoxy, OCH₂CH₂COOC(CH₃)₃,OCH₂CH₂COO(CH₂)₃—C₂H₅, OCH₂CH₂COO(CH₂)₄—C₂H₅, 2-(COOCH₃)propoxy,2-(COOC₂H₅)propoxy, 2-(COOCH₂—C₂H₅)propoxy, 2-[COOCH(CH₃)₂]propoxy,2-(COOCH₂CH₂—C₂H₅)propoxy, 2-(1-methylpropoxycarbonyl)propoxy,2-(2-methylpropoxycarbonyl)propoxy, 2-[COOC(CH₃)₃]propoxy,3-(COOCH₃)propoxy, 3-(COOC₂H₅)propoxy, 3-(COOCH₂—C₂H₅)propoxy,3-[COOCH(CH₃)₂]propoxy, 3-(COOCH₂CH₂—C₂H₅)propoxy,3-(1-methylpropoxycarbonyl)propoxy, 3-(2-methylpropoxycarbonyl)propoxy,3-[COOC(CH₃)₃]propoxy, 3-[COO(CH₂)₃—C₂H₅]propoxy,3-[COO(CH₂)₄—C₂H₅]propoxy, 2-(COOCH₃)butoxy, 2-(COOC₂H₅)butoxy,2-(COOCH₂—C₂H₅)butoxy, 2-[COOCH(CH₃)₂]butoxy, 2-(COOCH₂CH₂—C₂H₅)butoxy,2-(1-methylpropoxycarbonyl)butoxy, 2-(2-methylpropoxycarbonyl)butoxy,2-[COOC(CH₃)₃]butoxy, 3-(COOCH₃)butoxy, 3-(COOC₂H₅)butoxy,3-(COOCH₂—C₂H₅)butoxy, 3-[COOCH(CH₃)₂]butoxy, 3-(COOCH₂CH₂—C₂H₅)butoxy,3-(1-methylpropoxycarbonyl)butoxy, 3-(2-methylpropoxycarbonyl)butoxy,3-[COOC(CH₃)₃]butoxy, 4-(COOCH₃)butoxy, 4-(COOC₂H₅)butoxy,4-(COOCH₂—C₂H₅)butoxy, 4-[COOCH(CH₃)₂]butoxy, 4-(COOCH₂CH₂—C₂H₅)butoxy,4-(1-methylpropoxycarbonyl)butoxy, 4-(2-methylpropoxycarbonyl)butoxy,4-[COOC(CH₃)₃]butoxy, 4-[COO(CH₂)₃—C₂H₅]butoxy,4-[COO(CH₂)₄—C₂H₅]butoxy, 5-(COOCH₃)pentoxy, 5-(COOC₂H₅)pentoxy,5-(COOCH₂—C₂H₅)pentoxy, 5-[COOCH(CH₃)₂]pentoxy,5-(COOCH₂CH₂—C₂H₅)pentoxy, 5-(1-methylpropoxycarbonyl)pentoxy,5-(2-methylpropoxycarbonyl)pentoxy, 5-[COOC(CH₃)₃]pentoxy,5-[COO(CH)₃—C₂H₅]pentoxy, 5-[COO(CH₂)₄—C₂H₅]pentoxy, 6-(COOCH₃)hexoxy,6-(COOC₂H₅)hexoxy, 6-(COOCH₂—C₂H₅)hexoxy, 6-[COOCH(CH₃)₂)hexoxy,6-(COOCH₂CH₂—C₂H₅)hexoxy, 6-(1methylpropoxycarbonyl)hexoxy,6-(2-methylpropoxycarbonyl)hexoxy, 6-[COOC(CH₃)₃]hexoxy,6-(COO(CH₂)₃—C₂H₅]hexoxy or 6-[COO(CH₂)₄—C₂H₅]hexoxy, in particularOCH₂COOCH₃, OCH₂COOCH(CH₃)₂, OCH(CH₃)COOCH₃ or OCH₂CH₂COOCH₃;

C₁-C₆-alkylsulfinyl: for example SOCH₃, SOC₂H₅, SOCH₂—C₂H₅, SOCH(CH₃)₂,n-butylsulfinyl, SOCH(CH₃)—C₂H₅—SOCH₂—CH(CH₃)₂, SOC(CH₃)₃,n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,1-ethylpropylsulfinyl, n-Hexylsulfinyl, 1,1-dimethylpropylsulfinyl,1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl,2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl,1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, inparticular SOCH₃ or SOC₂H₅;

C₁-C₆-alkylsulfonyl: for example SO₂CH₃, SO₂C₂H₅, SO₂CH₂—C₂H₅,SO₂CH(CH₃)₂, n-butylsulfonyl, SO₂CH(CH₃)—C₂H₅, SO₂CH₂—CH(CH₃)₂,SO₂C(CH₃)₃, n-pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, inpart icular SO₂CH₃ or SO₂C₂H₅;

C₁-C₆-haloalkylsulfonyl: C₁-C₆-alkylsulfonyl as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, i.e., for example, ClCH₂—SO₂—, CH(Cl)₂—SO₂—, C(Cl)₃—SO₂—,FCH₂—SO₂—, CHF₂—SO₂—, CF₃—SO₂—, chlorofluoromethyl-SO₂—, dichlorofluoromethyl-SO₂—, chlorodifluoromethyl-SO₂—, 1-fluoroethyl-SO₂—,2-fluoroethyl-SO₂—, 2-chloroethyl-SO₂—, 2-bromoethyl-SO₂—,2-iodoethyl-SO₂—, 2,2-difluoroethyl-SO₂—, 2,2,2-trifluoroethyl-SO₂—,2-chloro-2-fluoroethyl-SO₂—, 2-chloro-2,2-difluoroethyl-SO₂—,2,2-dichloro-2-fluoroethyl-SO₂—, 2,2,2-trichloroethyl-SO₂—, C₂F₅—SO₂—,2-fluoropropyl-SO₂—, 3-fluoropropyl-SO₂—, 2,2-difluoropropyl-SO₂—,2,3-difluoropropyl-SO₂—, 2-chloropropyl-SO₂—, 3-chloropropyl-SO₂—,2,3-dichloropropyl-SO₂—, 2-bromopropyl-SO₂—, 3-bromopropyl-SO₂—,3,3,3-trifluoropropyl-SO₂—, 3,3,3-trichloropropyl-SO₂—,2,2,3,3,3-pentafluoropropyl-SO₂—, C₂F₅—CF₂—SO₂—,1-(fluoromethyl)-2-fluoroethyl-SO₂—,1-(chloromethyl)-2-chloroethyl-SO₂—, 1-(bromomethyl)-2-bromoethyl-SO₂—,4-fluorobutyl-SO₂—, 4-chlorobutyl-SO₂—, 4-bromobutyl-SO₂—,C₂F₅—CF₂—CF₂—SO₂—, 5-fluoropentyl-SO₂—, 5-chloropentyl-SO₂—,5-bromopentyl-SO₂—, 5-iodopentyl-SO₂—, 5,5,5-trichloropentyl-SO₂—,C₂F₅—CF₂—CF₂-CF₂—SO₂—, 6-fluorohexyl-SO₂—, 6-chlorohexyl-SO₂—,6-bromohexyl-SO₂—, 6-iodohexyl-SO₂—, 6,6,6-trichlorohexyl-SO₂— ordodecafluorohexyl-SO₂—, in particular CF₃—SO₂—;

C₃-C₆-alkenyl: for example prop-1-en-1-yl, allyl, 1-methylethenyl,n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl,2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl,1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl,n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl,1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl,4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl,2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl,1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl,1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl,1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl,2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl,2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl,3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl,2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl,1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or1-ethyl-2-methylprop-2-en-1-yl, in particular allyl;

C₃-C₆-alkynyl: for example prop-1-yn-1-yl, propargyl, n-but-1-yn-1-yl,n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl,n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl,n-pent-2-yn-4-yl, n-pent-2-in-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl,n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl,n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl,3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl,4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particularpropargyl;

C₃-C₆-alkenyloxy: for example prop-1-en-1-yloxy, allyloxy,1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy,n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy,n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy,n-hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy,2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy,4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy,2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy,4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy,2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy,4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy,2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy,4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy,1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy,1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy,1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy,1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy,2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy,2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy,3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy,1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy,2-ethylbut-2-en-1-yloxy, 2-ethylbut-2-en-1-yloxy,2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy,1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or1-ethyl-2-methylprop-2-en-1-yloxy, in particular allyloxy;

C₃-C₆-alkynyloxy: for example prop-1-yn-1-yloxy, propargyloxy,n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy,n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy,n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy,n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy,3-methyl-but-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy,n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy,n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy,n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy,3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy,3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy,4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or4-methylpent-2-yn-5-yloxy, in particular propargyloxy.

With a view to the use of the substituted 2-phenylpyridine I asherbicides and/or as compounds having desiccant/defoliant action, thevariables preferably have the following meanings, in each case on theirown or in combination:

n is zero;

R¹ is C₁-C₆-alkylsulfonyl, in particular SO₂CH₃;

R² is halogen, in particular chlorine;

R³ is hydrogen, fluorine or chlorine, particularly preferably fluorineor chlorine, in particular fluorine;

R⁴ is cyano or halogen, particularly preferably cyano or chlorine, inparticular chlorine;

R⁵ is hydrogen, nitro, cyano, hydroxylamino, C₁-C₆-alkyl (in particularCH₃), C₁-C₆-haloalkyl (in particular halomethyl), —COCl, —CO—OR⁶,—CCO—O—(C₁-C₄-alkylene)—CO—OR⁶, —O—(C₁-C₄-alkylene)—CO—OR⁶,—O—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —COR⁹, formyl,—CH═N—OR¹⁵ or —CNH₂, particularly preferably —CO—OR⁶,—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CO—(C₁-C₄-alkylene)—CO—OR⁶ or —OR⁹;

R⁶ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl orC₁-C₆-alkoxy-C₁-C₆-alkyl;

R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl;

R¹⁵ is C₁-C₆-alkyl.

Very particular preference is given to the compounds of the formula Ia({circumflex over (=)}I where n=zero; R¹=methylsulfonyl; R² andR⁴=chlorine; R³=fluorine), in particular to the compounds of Table 1:

TABLE 1 Ia

No. R⁵ Ia.1 —H Ia.2 —F Ia.3 —Cl Ia.4 —Br Ia.5 —I Ia.6 —CN Ia.7 —CH₃ Ia.8—CH₂Cl Ia.9 —CHCl₂ Ia.10 —CCl₃ Ia.11 —CH₂Br Ia.12 —CHBr₂ Ia.13 —COClIa.14 —CO—OH Ia.15 —CO—OCH₃ Ia.16 —CO—OC₂H₅ Ia.17 —CO—OCH₂—C₂H₅ Ia.18—CO—OCH(CH₃)₂ Ia.19 —CO—OCH₂—CH₂—C₂H₅ Ia.20 —CO—OCH₂—CH(CH₃)₂ Ia.21—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.22 —CO—OCH₂—CCl₃ Ia.23 —CO—OCH₂—CF₃ Ia.24—CO—OCH₂—CH═CH₂ Ia.25 —CO—OCH₂—CH═CH—CH₃ Ia.26 —CO—OCH₂—CH₂—CH═CH₂ Ia.27—CO—OCH(CH₃)—CH═CH₂ Ia.28 —CO—OCH₂—CH₂—CH₂—CH═CH₂ Ia.29—CO—OCH₂—CH═C(CH₃)₂ Ia.30 —CO—OCH₂—C(CH₃)═CH—CH₃ Ia.31 —CO—OCH₂—C≡CHIa.32 —CO—OCH(CH₃)—C≡CH Ia.33 —CO—OCH₂—C≡C—CH₃ Ia.34 —CO—OCH₂—C≡C—C₂H₅Ia.35 —CO—O-cyclopropyl Ia.36 —CO—O-cyclobutyl Ia.37 —CO—O-cyclopentylIa.38 —CO—O-cyclohexyl Ia.39 —CO—OCH₂—CH₂—OCH₃ Ia.40 —CO—OCH₂—CH₂—OC₂H₅Ia.41 —CO—OCH₂—CH₂—OCH₂—CH₂—CH₃ Ia.42 —CO—OCH₂—CH₂—OCH(CH₃)₂ Ia.43—CO—NH₂ Ia.44 —CO—NH—CH₃ Ia.45 —CO—N(CH₃)₂ Ia.46 —CO—NH—CH₂—CO—OH Ia.47—CO—NH—CH₂—CO—OCH₃ Ia.48 —CO—NH—CH₂—CO—OC₂H₅ Ia.49—CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.50 —CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.51—CO—NH—CH(CH₃)—CO—OH Ia.52 —CO—NH—CH(CH₃)—CO—OCH₃ Ia.53—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.54 —CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.55—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.56 —CO—N(CH₃)—CH₂—CO—OH Ia.57—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.58 —CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.59—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.60 —CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.61—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.62 —CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.63—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.64 —CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.65—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.66 —CO—OCH₂—CO—OH Ia.67—CO—OCH₂—CO—OCH₃ Ia.68 —CO—OCH₂—CO—OC₂H₅ Ia.69 —CO—OCH₂—CO—OCH₂—C₂H₅Ia.70 —CO—OCH₂—CO—OCH(CH₃)₂ Ia.71 —CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.72—CO—OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.73 —CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.74—CO—OCH₂—CO—OC(CH₃)₃ Ia.75 —CO—OCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.76—CO—OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.77 —CO—OCH(CH₃)—CO—OH Ia.78—CO—OCH(CH₃)—CO—OCH₃ Ia.79 —CO—OCH(CH₃)—CO—OC₂H₅ Ia.80—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.81 —CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.82—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.83 —CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.84—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.85 —CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.86—CO—OCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.87—CO—OCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.88 —CO—OCH₂—CO—NH₂ Ia.89—CO—OCH₂—CO—NH—CH₃ Ia.90 —CO—OCH₂—CO—N(CH₃)₂ Ia.91—CO—OCH₂—CO—N(CH₃)—CH₂—CO—OH Ia.92 —CO—OCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.93—CO—OCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.94 —CO—OCH(CH₃)—CO—NH₂ Ia.95—CO—OCH(CH₃)—CO—NH—CH₃ Ia.96 —CO—OCH(CH₃)—CO—N(CH₃)₂ Ia.97—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.98—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.99—CO—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.100 —OCH₂—CHO Ia.101 —OCH₂—CO—CH₃Ia.102 —OCH₂—CO—C₂H₅ Ia.103 —OCH₂—CO—CH(CH₃)₂ Ia.104 —OCH₂—CO—CH₂—C₂H₅Ia.105 —OCH₂—CO—CH₂—CH₂—C₂H₅ Ia.106 —OCH₂—CO—CH₂—CH(CH₃)₂ Ia.107—OCH₂—CO—CH(CH₃)—C₂H₅ Ia.108 —OCH₂—CO—C(CH₃)₃ Ia.109 —OCH(CH₃)—CO—CH₃Ia.110 —OCH(CH₃)—CO—C₂H₅ Ia.111 —OCH(CH₃)—CO—CH₂—C₂H₅ Ia.112—OCH(CH₃)—CO—CH(CH₃)₂ Ia.113 —OCH(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.114—OCH(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.115 —OCH(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.116—OCH(CH₃)—CO—C(CH₃)₃ Ia.117 —OCH₂—CO—CH₂—Cl Ia.118 —OCH(CH₃)—CO—CH₂—ClIa.119 —OCH₂—CO—CH₂—CH═CH₂ Ia.120 —OCH(CH₃)—CO—CH₂—CH═CH₂ Ia.121—OCH₂—CO—CH₂—C≡CH Ia.122 —OCH(CH₃)—CO—CH₂—C≡CH Ia.123—OCH₂—CO-cyclopentyl Ia.124 —OCH(CH₃)—CO-cyclohexyl Ia.125—OCH₂—CO—CH₂—OCH₃ Ia.126 —OCH(CH₃)—CO—CH₂—OCH₃ Ia.127 —OCH₂—CO—CH₂—OC₂H₅Ia.128 —OCH(CH₃)—CO—CH₂—OC₂H₅ Ia.129 —OCH₂—CO—CH₂—CH₂—OCH₃ Ia.130—OCH(CH₃)—CO—CH₂—CH₂—OCH₃ Ia.131 —OCH₂—CO—CH₂—CH₂—OC₂H₅ Ia.132—OCH(CH₃)—CO—CH₂—CH₂—OC₂H₅ Ia.133 —SCH₂—CHO Ia.134 —SCH₂—CO—CH₃ Ia.135—SCH₂—CO—C₂H₅ Ia.136 —SCH₂—CO—CH(CH₃)₂ Ia.137 —SCH₂—CO—CH₂—C₂H₅ Ia.138—SCH(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.139 —SCH(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.140—SCH(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.141 —SCH(CH₃)—CO—C(CH₃)₃ Ia.142—SCH₂—CO—CH₂—CH═CH₂ Ia.143 —SCH(CH₃)—CO—CH₂—CH═CH₂ Ia.144—SCH₂—CO—CH₂—CH≡CH Ia.145 —SCH(CH₃)—CO—CH₂—CH≡CH Ia.146—SCH₂—CO-cyclopentyl Ia.147 —SCH(CH₃)—CO-cyclopentyl Ia.148—SCH₂—CO-cyclohexyl Ia.149 —SCH(CH₃)—CO-cyclohexyl Ia.150—SCH₂—CO—CH₂—OCH₃ Ia.151 —SCH(CH₃)—CO—CH₂—OCH₃ Ia.152 —SCH₂—CO—CH₂—OC₂H₅Ia.153 —SCH(CH₃)—CO—CH₂—OC₂H₅ Ia.154 —SCH₂—CO—CH₂—CH₂—OCH₃ Ia.155—SCH(CH₃)—CO—CH₂—CH₂—OCH₃ Ia.156 —SCH₂—CO—CH₂—CH₂—OC₂H₅ Ia.157—SCH(CH₃)—CO—CH₂—CH₂—OC₂H₅ Ia.158 —OCH₂—CO—OH Ia.159 —OCH₂—CO—OCH₃Ia.160 —OCH₂—CO—OC₂H₅ Ia.161 —OCH₂—CO—OCH₂—C₂H₅ Ia.162—OCH₂—CO—OCH(CH₃)₂ Ia.163 —OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.164—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.165 —OCH₂—CO—OC(CH₃)₃ Ia.166—OCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.167 —OCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.168—OCH(CH₃)—CO—OH Ia.169 —OCH(CH₃)—CO—OCH₃ Ia.170 —OCH(CH₃)—CO—OC₂H₅Ia.171 —OCH(CH₃)—CO—OCH₂—OC₂H₅ Ia.172 —OCH(CH₃)—CO—OCH(CH₃)₂ Ia.173—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.174 —OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.175—OCH(CH₃)—CO—OC(CH₃)₃ Ia.176 —OCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.177—OCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.178 —SCH₂—CO—OH Ia.179 —SCH₂—CO—OCH₃Ia.180 —SCH₂—CO—OC₂H₅ Ia.181 —SCH₂—CO—OCH₂—C₂H₅ Ia.182—SCH₂—CO—OCH(CH₃)₂ Ia.183 —SCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.184—SCH₂—CO—OCH₂—CH(CH₃)₂ Ia.185 —SCH₂—CO—OC(CH₃)₃ Ia.186—SCH₂—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.187 —SCH₂—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.188—SCH(CH₃)—CO—OH Ia.189 —SCH(CH₃)—CO—OCH₃ Ia.190 —SCH(CH₃)—CO—OC₂H₅Ia.191 —SCH(CH₃)—CO—OCH₂—C₂H₅ Ia.192 —SCH(CH₃)—CO—OCH(CH₃)₂ Ia.193—SCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.194 —SCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.195—SCH(CH₃)—CO—OC(CH₃)₃ Ia.196 —SCH(CH₃)—CO—OCH₂—CH₂—CH₂—C₂H₅ Ia.197—SCH(CH₃)—CO—OCH₂—CH₂—CH(CH₃)₂ Ia.198 —OCH₂—CO—OCH₂—CO—OH Ia.199—OCH₂—CO—OCH₂—CO—OCH₃ Ia.200 —OCH₂—CO—OCH₂—CO—OC₂H₅ Ia.201—OCH₂—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.202 —OCH₂—CO—OCH₂—CO—OCH(CH₃)₂ Ia.203—OCH₂—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.204 —OCH₂—CO—OCH₂—CO—OCH₂—CH(CH₃)₂Ia.205 —OCH₂—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.206 —OCH₂—CO—OCH₂—CO—OC(CH₃)₃Ia.207 I>—OCH₂—CO—OCH(CH₃)—CO—OH Ia.208 —OCH₂—CO₂—CH(CH₃)—CO—OCH₃ Ia.209—OCH₂—CO—OCH(CH₃)—CO—OC₂H₅ Ia.210 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.211—OCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.212 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.213 —OCH₂—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.214—OCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.215 —OCH₂—CO—OCH(CH₃)—CO—OC(CH₃)₃Ia.216 —OCH(CH₃)—CO—OCH₂—CO—OH Ia.217 —OCH(CH₃)—CO—OCH₂—CO—OCH₃ Ia.218—OCH(CH₃)—CO—OCH₂—CO—OC₂H₅ Ia.219 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.220—OCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)₂ Ia.221 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅Ia.222 —OCH(CH₃)—CO—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.223—OCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.224 —OCH(CH₃)—CO—OCH₂—CO—OC(CH₃)₃Ia.225 —OCH(CH₃)—CO—OCH(CH₃)—CO—OH Ia.226 —OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₃Ia.227 —OCH(CH₃)—CO—OCH(CH₃)—CO—OC₂H₅ Ia.228—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.229—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.230—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.231—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.232—OCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.233—OCH(CH₃)—CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.234 —SCH₂—CO—OCH₂—CO—OH Ia.235—SCH₂—CO—OCH₂—CO—OCH₃ Ia.236 —SCH₂—CO—OCH₂—CO—OC₂H₅ Ia.237—SCH₂—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.238 —SCH₂—CO—OCH₂—CO—OCH(CH₃)₂ Ia.239—SCH₂—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅ Ia.240 —SCH₂—CO—OCH₂—CO—OCH₂—CH(CH₃)₂Ia.241 —SCH₂—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.242 —SCH₂—CO—OCH₂—CO—OC(CH₃)₃Ia.243 —SCH₂—CO—OCH(CH₃)—CO—OH Ia.244 —SCH₂—CO—OCH(CH₃)—CO—OCH₃ Ia.245—SCH₂—CO—OCH(CH₃)—CO—OC₂H₅ Ia.246 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.247—SCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.248 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.249 —SCH₂—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.250—SCH₂—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.251 —SCH₂—CO—OCH(CH₃)—CO—OC(CH₃)₃Ia.252 —SCH(CH₃)—CO—OCH₂—CO—OH Ia.253 —SCH(CH₃)—CO—OCH₂—CO—OCH₃ Ia.254—SCH(CH₃)—CO—OCH₂—CO—OC₂H₅ Ia.255 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—C₂H₅ Ia.256—SCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)₂ Ia.257 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—CH₂—C₂H₅Ia.258 —SCH(CH₃)—CO—OCH₂—CO—OCH₂—CH(CH₃)₂ Ia.259—SCH(CH₃)—CO—OCH₂—CO—OCH(CH₃)—C₂H₅ Ia.260 —SCH(CH₃)—CO—OCH₂—CO—OC(CH₃)₃Ia.261 —SCH(CH₃)—CO—OCH(CH₃)—CO—OH Ia.262 —SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₃Ia.263 —SCH(CH₃)—CO—OCH(CH₃)—CO—OC₂H₅ Ia.264—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.265—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)₂ Ia.266—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.267—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH₂—CH(CH₃)₂ Ia.268—SCH(CH₃)—CO—OCH(CH₃)—CO—OCH(CH₃)—C₂H₅ Ia.269—SCH(CH₃)—CO—OCH(CH₃)—CO—OC(CH₃)₃ Ia.270 —OCH₂—CO—NH₂ Ia.271—OCH₂—CO—NH—CH₃ Ia.272 —OCH₂—CO—N(CH₃)₂ Ia.273 —OCH₂—CO—NH—CH₂—CO—OHIa.274 —OCH₂—CO—NH—CH₂—CO—OCH₃ Ia.275 —OCH₂—CO—NH—CH₂—CO—OC₂H₅ Ia.276—OCH₂—CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.277 —OCH₂—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅Ia.278 —OCH₂—CO—NH—CH(CH₃)—CO—OH Ia.279 —OCH₂—CO—NH—CH(CH₃)—CO—OCH₃Ia.280 —OCH₂—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.281—OCH₂—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.282—OCH₂—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.283 —OCH₂—CO—N(CH₃)—CH₂—CO—OHIa.284 —OCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.285 —OCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅Ia.286 —OCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.287—OCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.288—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.289 —OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₃Ia.290 —OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.291—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.292—OCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.293 —OCH(CH₃)—CO—NH₂ Ia.294—OCH(CH₃)—CO—NH—CH₃ Ia.295 —OCH(CH₃)—CO—N(CH₃)₂ Ia.296—OCH(CH₃)—CO—NH—CH₂—CO—OH Ia.297 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.298—OCH(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.299 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₂—C₂H₅Ia.300 —OCH(CH₃)—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.301—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OH Ia.302 —OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃Ia.303 —OCH(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.304—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.305—OCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.306—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.307 —OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃Ia.308 —OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.309—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.310—OCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.311—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.312—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.313—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.314—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.315—OCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.316 —SCH₂—CO—NH₂ Ia.317—SCH₂—CO—NH—CH₃ Ia.318 —SCH₂—CO—N(CH₃)₂ Ia.319 —SCH₂—CO—NH—CH₂—CO—OHIa.320 —SCH₂—CO—NH—CH₂—CO—OCH₃ Ia.321 —SCH₂—CO—NH—CH₂—CO—OC₂H₅ Ia.322—SCH₂—CO—NH—CH₂—CO—OCH₂—C₂H₅ Ia.323 —SCH₂—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅Ia.324 —SCH₂—CO—NH—CH(CH₃)—CO—OH Ia.325 —SCH₂—CO—NH—CH(CH₃)—CO—OCH₃Ia.326 —SCH₂—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.327—SCH₂—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.328—SCH₂—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.329 —SCH₂—CO—N(CH₃)—CH₂—CO—OHIa.330 —SCH₂—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.331 —SCH₂—CO—N(CH₃)—CH₂—CO—OC₂H₅Ia.332 —SCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.333—SCH₂—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.334—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.335 —SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₃Ia.336 —SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.337—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.338—SCH₂—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.339 —SCH(CH₃)—CO—NH₂ Ia.340—SCH(CH₃)—CO—NH—CH₃ Ia.341 —SCH(CH₃)—CO—N(CH₃)₂ Ia.342—SCH(CH₃)—CO—NH—CH₂—CO—OH Ia.343 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.344—SCH(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.345 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₂—C₂H₅Ia.346 —SCH(CH₃)—CO—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.347—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OH Ia.348 —SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃Ia.349 —SCH(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.350—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.351—SCH(CH₃)—CO—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.352—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.353 —SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃Ia.354 —SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.355—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.356—SCH(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.357—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.358—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.359—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.360—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.361—SCH(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.362 —OH Ia.363 —OCH₃Ia.364 —OC₂H₅ Ia.365 —OCH₂—C₂H₅ Ia.366 —OCH(CH₃)₂ Ia.367 —OCH₂—CH₂—C₂H₅Ia.368 —OCH(CH₃)—C₂H₅ Ia.369 —OCH₂—CH(CH₃)₂ Ia.370 —OCH₂—CH₂—CH₂—C₂H₅Ia.371 —OCH₂—CH₂—CH(CH₃)—CH₃ Ia.372 —OCH₂—CF₃ Ia.373 —OCHF₂ Ia.374—OCH₂—CH═CH₂ Ia.375 —OCH₂—CH═CH—CH₃ Ia.376 —OCH₂—CH(CH₃)═CH₂ Ia.377—OCH(CH₃)—CH═CH₂ Ia.378 —OCH₂—CH═CH—C₂H₅ Ia.379 —OCH₂—CH₂—CH═CH—CH₃Ia.380 —OCH₂—CH₂—CH₂—CH═CH₂ Ia.381 —OCH₂—C≡CH Ia.382 —OCH(CH₃)—C≡CHIa.383 —OCH₂—C≡C—CH₃ Ia.384 —OCH₂—C≡C—C₂H₅ Ia.385 Cyclopropyloxy Ia.386Cyclobutyloxy Ia.387 Cyclopentyloxy Ia.388 Cyclohexyloxy Ia.389—OCH₂—CH₂—OCH₃ Ia.390 —OCH₂—CH₂—OC₂H₅ Ia.391 —OCH₂—CH₂—OCH₂—C₂H₅ Ia.392—OCH₂—CH₂—OCH(CH₃)₂ Ia.393 —SH Ia.394 —SCH₃ Ia.395 —SC₂H₅ Ia.396—SCH₂—C₂H₅ Ia.397 —SCH(CH₃)₂ Ia.398 —SCH₂—CH₂—C₂H₅ Ia.399 —SCH(CH₃)—C₂H₅Ia.400 —SCH₂—CH(CH₃)₂ Ia.401 —SCH₂—CH₂—CH₂—C₂H₅ Ia.402—SCH₂—CH₂—CH(CH₃)—CH₃ Ia.403 —SCH₂—CF₃ Ia.404 —SCHF₂ Ia.405 —SCH₂—CH═CH₂Ia.406 —SCH₂—CH═CH—CH₃ Ia.407 —SCH₂—CH(CH₃)═CH₂ Ia.408 —SCH(CH₃)—CH═CH₂Ia.409 —SCH₂—CH═CH—C₂H₅ Ia.410 —SCH₂—CH₂—CH═CH—CH₃ Ia.411—SCH₂—CH₂—CH₂—CH═CH₂ Ia.412 —SCH₂—C≡CH Ia.413 —SCH(CH₃)—C≡CH Ia.414—SCH₂—C≡C—CH₃ Ia.415 —SCH₂—C≡C—C₂H₅ Ia.416 Cyclopropylthio Ia.417Cyclobutylthio Ia.418 Cyclopentylthio Ia.419 Cyclohexylthio Ia.420—SCH₂—CH₂—OCH₃ Ia.421 —SCH₂—CH₂—OC₂H₅ Ia.422 —SCH₂—CH₂—OCH₂—C₂H₅ Ia.423—SCH₂—CH₂—OCH(CH₃)₂ Ia.424 —CH═CH₂—CO—OH Ia.425 —CH═CH₂—CO—OCH₃ Ia.426—CH═CH₂—CO—OC₂H₅ Ia.427 —CH═CH₂—CO—OCH₂—C₂H₅ Ia.428—CH═CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.429 —CH═CH(Cl)—CO—OH Ia.430—CH═CH(Cl)—CO—OCH₃ Ia.431 —CH═CH(Cl)—CO—OC₂H₅ Ia.432—CH═CH(Cl)—CO—OCH₂—C₂H₅ Ia.433 —CH═CH(Cl)—CO—OCH₂—CH₂—C₂H₅ Ia.434—CH═CH(CH₃)—CO—OH Ia.435 —CH═CH(CH₃)—CO—OCH₃ Ia.436 —CH═CH(CH₃)—CO—OC₂H₅Ia.437 —CH═CH(CH₃)—CO—OCH₂—C₂H₅ Ia.438 —CH═CH(CH₃)—CO—OCH₂—CH₂—C₂H₅Ia.439 —CH═CH—CO—NH₂ Ia.440 —CH═CH—CO—NH—CH₃ Ia.441 —CH═CH—CO—N(CH₃)₂Ia.442 —CH═CH—CO—NH—CH₂—CO—OH Ia.443 —CH═CH—CO—NH—CH₂—CO—OCH₃ Ia.444—CH═CH—CO—NH—CH₂—CO—OC₂H₅ Ia.445 —CH═CH—CO—NH—CH(CH₃)—CO—OH Ia.446—CH═CH—CO—NH—CH(CH₃)—CO—OCH₃ Ia.447 —CH═CH—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.448—CH═CH—CO—N(CH₃)—CH₂—CO—OH Ia.449 —CH═CH—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.450—CH═CH—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.451 —CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OHIa.452 —CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.453—CH═CH—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.454 —CH═C(Cl)—CO—NH—CH(CH₃)—CO—OHIa.455 —CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.456—CH═C(Cl)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.457 —CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OHIa.458 —CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.459—CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.460—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.461—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.462—CH═C(Cl)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.463 —CHO Ia.464 —CO—CH₃ Ia.465—CO—C₂H₅ Ia.466 —CO—CH₂—C₂H₅ Ia.467 —CO—CH(CH₃)₂ Ia.468 —CO—CH₂—CH₂—C₂H₅Ia.469 —CO—CH₂—CH(CH₃)—CH₃ Ia.470 —CO—CH(CH₃)—C₂H₅ Ia.471 —CO—CH₂—ClIa.472 —CO—CH₂—Br Ia.473 —CO—CHCl₂ Ia.474 —CO—CHBr₂ Ia.475 —CO—CCl₃Ia.476 —CO—CF₃ Ia.477 —CH═C(CH₃)—CO—NH₂ Ia.478 —CH═C(CH₃)—CO—NH—CH₃Ia.479 —CH═C(CH₃)—CO—N(CH₃)₂ Ia.480 —CH═C(CH₃)—CO—NH—CH₂—CO—OH Ia.481—CH═C(CH₃)—CO—NH—CH₂—CO—OCH₃ Ia.482 —CH═C(CH₃)—CO—NH—CH₂—CO—OC₂H₅ Ia.483—CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OH Ia.484 —CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OCH₃Ia.485 —CH═C(CH₃)—CO—NH—CH(CH₃)—CO—OC₂H₅ Ia.486—CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OH Ia.487 —CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OCH₃Ia.488 —CH═C(CH₃)—CO—N(CH₃)—CH₂—CO—OC₂H₅ Ia.489—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OH Ia.490—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.491—CH═C(CH₃)—CO—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.492 —CH═C(Cl)—CO—NH₂ Ia.493—CH—C(Cl)—CO—NH—CH₃ Ia.494 —CH═C(Cl)—CO—N(CH₃)₂ Ia.495—CH═C(Cl)—CO—NH—CH₂—CO—OH Ia.496 —CH═C(Cl)—CO—NH—CH₂—CO—OCH₃ Ia.497—CH═C(Cl)—CO—NH—CH₂—CO—OC₂H₅ Ia.498 —CO—CH₂—CH═CH₂ Ia.499—CO—CH₂—CH═CH—CH₃ Ia.500 —CO—CH₂—CH₂—CH═CH₂ Ia.501 —CO—CH₂—C≡CH Ia.502—CO—CH(CH₃)—C≡CH Ia.503 —CO—CH₂—C≡C—CH₃ Ia.504 CyclopropylcarbonylIa.505 Cyclobutylcarbonyl Ia.506 Cyclopentylcarbonyl Ia.507Cyclohexylcarbonyl Ia.508 —CO—CH₂—OCH₃ Ia.509 —CO—CH₂—OC₂H₅ Ia.510—CO—CH₂—CH₂—OCH₃ Ia.511 —CO—CH₂—CH₂—OC₂H₅ Ia.512 1,3-Dioxolan-2-ylIa.513 4-(CH₃)-1,3-dioxolan-2-yl Ia.514 4,5-(CH₃)₂-1,3-dioxolan-2-ylIa.515 4,4-(CH₃)₂-1,3-dioxolan-2-yl Ia.5164,4,5-(CH₃)₃-1,3-dioxolan-2-yl Ia.517 4,4,5,5-(CH₃)₄-1,3-dioxolan-2-ylIa.518 4-(COOCH₃)-1,3-dioxolan-2-yl Ia.519 4-(COOC₂H₅)-1,3-dioxolan-2-ylIa.520 4-(COOCH₂C₂H₅)-1,3-dioxolan-2-yl Ia.5214-[COOCH(CH₃)₂]-1,3-dioxolan-2-yl Ia.5224-(COOCH₂CH₂—C₂H₅)-1,3-dioxolan-2-yl Ia.5234-[COOCH₂CH(CH₃)₂]-1,3-dioxolan-2-yl Ia.5244-[COOCH(CH₃)C₂H₅]-1,3-dioxolan-2-yl Ia.5254-[COOC(CH₃)₃]-1,3-dioxolan-2-yl Ia.526 4,5-(COOCH₃)₂-1,3-dioxolan-2-ylIa.527 4,5-(COOC₂H₅)₂-1,3-dioxolan-2-yl Ia.528

Ia.529 1,3-Dithiolan-2-yl Ia.530 4-(CH₃)-1,3-dithiolan-2-yl Ia.5314,5-(CH₃)₂-1,3-dithiolan-2-yl Ia.532 4,4-(CH₃)₂-1,3-dithiolan-2-ylIa.533 4-(COOCH₃)-1,3-dithiolan-2-yl Ia.5344-(COOC₂H₅)-1,3-dithiolan-2-yl Ia.535 4-(COOCH₂C₂H₅)-1,3-dithiolan-2-ylIa.536 4-[COOCH(CH₃)₂]-1,3-dithiolan-2-yl Ia.5374-(COOCH₂CH₂C₂H₅)-1,3-dithiolan-2-yl Ia.5384-[COOCH₂CH(CH₃)₂]-1,3-dithiolan-2-yl Ia.5394-[COOCH(CH₃)C₂H₅]-1,3-dithiolan-2-yl Ia.5404-[COOC(CH₃)₃]-1,3-dithiolan-2-yl Ia.5414,5-(COOCH₃)₂-1,3-dithiolan-2-yl Ia.5424,5-(COOC₂H₅)₂-1,3-dithiolan-2-yl Ia.543 —CH═N—OH Ia.544 —CH═N—OCH₃Ia.545 —CH═N—OC₂H₅ Ia.546 —CH═N—OCH₂—C₂H₅ Ia.547 —CH═N—OCH(CH₃)₂ Ia.548—CH═N—OCH₂—CH₂—C₂H₅ Ia.549 —CH═N—OCH₂—CH(CH₃)₂ Ia.550—CH═N—OCH(CH₃)—C₂H₅ Ia.551 —CH═N—OC(CH₃)₃ Ia.552 —CH═N—OCH₂—CH₂—CH₂—C₂H₅Ia.553 —CH═N—OCH₂—CH₂—CH(CH₃)₂ Ia.554 —CH═N—OCH₂—CO—OCH₃ Ia.555—CH═N—OCH₂—CO—OC₂H₅ Ia.556 —CH═N—OCH₂—CO—OCH₂—C₂H₅ Ia.557—CH═N—OCH(CH₃)—CO—OCH₃ Ia.558 —CH═N—OCH(CH₃)—CO—OC₂H₅ Ia.559—CH═N—OCH(CH₃)—CO—OCH₂—C₂H₅ Ia.560 —CH(OCH₃)₂ Ia.561 —CH(OC₂H₅)₂ Ia.562—CH(OCH₂—C₂H₅)₂ Ia.563 —CH(OCH₂—CH₂—C₂H₅)₂ Ia.564 —NO₂ Ia.565 —NH—OHIa.566 —NH₂ Ia.567 —NH—CH₃ Ia.568 —N(CH₃)₂ Ia.569 —NH—CH₂—CO—OCH₃ Ia.570—NH—CH₂—CO—OC₂H₅ Ia.571 —NH—CH₂—CO—OCH₂—C₂H₅ Ia.572—NH—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.573 —NH—CH(CH₃)—CO—OCH₃ Ia.574—NH—CH(CH₃)—CO—OC₂H₅ Ia.575 —NH—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.576—NH—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.577 —N(CH₃)—CH₂—CO—OCH₃ Ia.578—N(CH₃)—CH₂—CO—OC₂H₅ Ia.579 —N(CH₃)—CH₂—CO—OCH₂—C₂H₅ Ia.580—N(CH₃)—CH₂—CO—OCH₂—CH₂—C₂H₅ Ia.581 —N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.582—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.583 —N(CH₃)—CH(CH₃)—CO—OCH₂—C₂H₅ Ia.584—N(CH₃)—CH(CH₃)—CO—OCH₂—CH₂—C₂H₅ Ia.585 —NH—SO₂—CH₃ Ia.586 —NH—SO₂—C₂H₅Ia.587 —NH—SO₂—CH₂—C₂H₅ Ia.588 —NH—SO₂—CH(CH₃)₂ Ia.589—NH—SO₂—CH₂—CH₂—C₂H₅ Ia.590 —NH—SO₂—CH₂—CH(CH₃)₂ Ia.591—NH—SO₂—CH(CH₃)—C₂H₅ Ia.592 —N(CH₃)—SO₂—CH₃ Ia.593 —N(CH₃)—SO₂—C₂H₅Ia.594 —N(CH₃)—SO₂—CH₂—C₂H₅ Ia.595 —N(CH₃)—SO₂—CH(CH₃)₂ Ia.596—N(CH₃)—SO₂—CH₂—CH₂—C₂H₅ Ia.597 —N(CH₃)—SO₂—CH₂—CH(CH₃)₂ Ia.598—NH—CO—CH₃ Ia.599 —NH—CO—C₂H₅ Ia.600 —NH—CO—CH₂—C₂H₅ Ia.601—NH—CO—CH(CH₃)₂ Ia.602 —NH—CO—CH₂—CH₂—C₂H₅ Ia.603 —NH—CO—CH₂—CH(CH₃)₂Ia.604 —NH—CO—CH(CH₃)—C₂H₅ Ia.605 —NH—CO—C(CH₃)₃ Ia.606 —N(CH₃)—CO—CH₃Ia.607 —N(CH₃)—CO—C₂H₅ Ia.608 —N(CH₃)—CO—CH₂—C₂H₅ Ia.609—N(CH₃)—CO—CH(CH₃)₂ Ia.610 —N(CH₃)—CO—CH₂—CH₂—C₂H₅ Ia.611—N(CH₃)—CO—CH₂—CH(CH₃)₂ Ia.612 —N(CH₃)—CO—CH(CH₃)—C₂H₅ Ia.613—N(CH₃)—CO—C(CH₃)₃ Ia.614 —SO₂—Cl Ia.615 —SO₂—OH Ia.616 —SO₂—NH₂ Ia.617—SO₂—NH—CH₃ Ia.618 —SO₂—N(CH₃)₂ Ia.619 —SO₂—NH—CH₂—CO—OCH₃ Ia.620—SO₂—NH—CH₂—CO—OC₂H₅ Ia.621 —SO₂—NH—CH(CH₃)—CO—OCH₃ Ia.622—SO₂—NH—CH(CH₃)—CO—OC₂H₅ Ia.623 —SO₂—N(CH₃)—CH₂—CO—OCH₃ Ia.624—SO₂—N(CH₃)—CH₂—CO—OC₂H₅ Ia.625 —SO₂—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.626—SO₂—N(CH₃)—CH(CH₃)—CO—OC₂H₅ Ia.627 1,3-Dioxan-2-yl Ia.6284-(CH₃)-1,3-dioxan-2-yl Ia.629 5-(CH₃)-1,3-dioxan-2-yl Ia.6305,5-(CH₃)₂-1,3-dioxan-2-yl Ia.631

Ia.632 1,3-Dithian-2-yl Ia.633 4-(CH₃)-dithian-2-yl Ia.6345-(CH₃)-dithian-2-yl Ia.635 5,5-(CH₃)₂-dithian-2-yl Ia.636OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.637 OCH(CH₃)—CO—OCH₂—CH═CH₂

Furthermore, very particular preference is given to the substituted2-phenylpyridines of the formulae Ib, Ic, Id, Ie and If, in particularto

the compounds Ib.1 to Ib.637, which differ from the correspondingcompounds Ia.1 to Ia.637 only in that R³ is chlorine:

the compounds Ic.1 to Ic.637, which differ from the correspondingcompounds Ia.1 to Ia.637 only in that R³ is hydrogen:

the compounds Id.1 to Id.637, which differ from the correspondingcompounds Ia.1 to Ia.637 only in that R⁴ is cyano:

the compounds Ie.1 to Ie.637, which differ from the correspondingcompounds Ia.1 to Ia.637 only in that R³ is chlorine and R⁴ is cyano:

the compounds If.1 to If.637, which differ from the correspondingcompounds Ia.1 to Ia.637 only in that R³ is hydrogen and R⁴ is cyano:

The substituted 2-phenylpyridines of the formula I can be obtained bydifferent routes, for example by one of the following processes:

Process A)

Oxidation of substituted 2-phenylpyridines of the formula I where n iszero and R¹ and R⁵ do not contain any oxidizable sulfur, in the mannerknown per se {cf., for example, A. Albini & S. Pietra, HeterocyclicN—Oxides, CRC-Press Inc., Boca Raton, USA 1991; H. S. Mosher et al.,Org. Synth. Coll. Vol. IV 1963, page 828; E. C. Taylor et al., Org.Synth. Coll. Vol. IV 1963, page 704; T. W. Bell et. al., Org. Synth. 69,page 226 (1990)}:

Among the oxidizing agents which are customary for oxidizing thepyridine ring, peracetic acid, trifluoroperacetic acid, perbenzoic acid,m-chloroperbenzoic acid, monopermaleic acid, magnesium monoperphthalate,sodium perborate, oxone® (contains peroxydisulfate) pertungstic acid andhydrogen peroxide may be mentioned by way of example.

Suitable solvents are, for example, water, sulfuric acid, carboxylicacids, such as acetic acid and trifluoroacetic acid, and alsohalogenated hydrocarbons, such as dichloromethane and chloroform.

The oxidation usually succeeds at temperatures from 0° C. to the boilingpoint of the reaction mixture.

The oxidizing agent is usually employed in at least equimolar amounts,based on the starting material. In general, an excess of oxidizing agenthas been found to be particularly advantageous.

Process B)

Transition-metal-catalyzed crosscoupling reaction of 2-halopyridines II(Hal=chlorine or bromine) with organometallic compounds of the formulaIII in the manner known per se {cf., for example, WO 95/02580 and theliterature cited therein on pages 21 and 22}:

M¹ is B(OH)₂, Mg—Cl, Mg—Br, Mg—I, Zn—Cl, Zn—Br, Zn—I, lithium, copper ortri(C₁-C₄-alkyl)tin, preferably B(OH)₂, Mg—Cl, Mg—Br, Mg—I, Zn—Cl, Zn—Bror Zn—I.

Alternatively, instead of the boronic acids III {M¹=B(OH)₂}, it is alsopossible to use the boroxines IV:

Suitable catalysts are, in particular, palladium catalysts, such astetrakis(triphenylphosphine)palladium(O),bis(triphenylphosphine)palladium(II) chloride,1,4-bis(diphenylphosphino)butanepalladium(II) chloride,1,2-bis(diphenylphosphino)ethanepalladium(II) chloride, palladium(II)acetate+triphenylphosphine, palladium(II)acetate+tri(o-tolyl)phosphineor palladium on activated carbon, and nickel catalysts, such asbis(triphenylphosphine)nickel(II) chloride,1,3-bis(diphenylphosphino)propanenickel(II) chloride or nickel(II)acetylacetonate.

Process C)

Diazotization of 5-amino-2-phenylpyridines V, reaction of the diazoniumsalts with acetic anhydride, hydrolysis of VI to give5-hydroxy-2-phenylpyridine VII and reaction of VII with R¹—L, where L isa suitable leaving group, such as chloride (in the case ofR¹=C₁-C₆-alkylsulfonyl):

Reactions of this type are generally known, for example from thefollowing publications (diazotization of aminopyridines usingisoamylnitrite): C. S. Giam et al., J. Chem. Soc., Chem. Commun. 16, 756(1980); T. Yasumitsu et al., J. Org. Chem. 46, 3564-3567 (1981).

The 5-amino-2-phenylpyridines of the formula V are known from WO98/07700 or can be obtained in the manner described therein.

5-Amino-2-(4-chloro-3-methoxyphenyl)pyridine and5-amino-2-(4-chloro-3-methoxyphenyl)-3-chloropyridine have already beendisclosed in WO 95/02580.

Process D)

Reaction of 5-hydroxy-2-phenylpyridines VIII with a C₁-C₆-alkylsulfinylchloride R¹—SO—Cl in a manner known per se {cf., for example, J.Hendrickson & P. Skipper, Tetrahedron 32, 1627 (1976); Th. Netscher & H.Prinzbach, Synthesis 8, 683-688 (1987); Y. F. Zhang et al., Inorg. Chem.31, 492-494 (1992), M. Jung & T. Lazarova, Tetrahedron Letters 37, 7-8(1996)}:

Process E)

Oxidation of substituted 2-phenylpyridines of the formula I in which R¹is C₁-C₆-alkylsulfinyl and the substituent R⁵ does not contain anyoxidizable sulfur, in a manner known per se {cf., for example, Th.Squires et al., J. Org. Chem. 46, 2373-2376 (1981) and Th. Netscher & H.Prinzbach, Synthesis 8, 683-688 (1987)}:

For suitable solvents, reaction temperatures and ratios, reference ismade to the details given under Process A). In addition to the oxidizingagents mentioned under Process A), alkali metal hypohalides, such assodium hypochloride and potassium hydrochloride, are also suitable here.

The substituted 2-phenylpyridines I can usually be prepared by one ofthe abovementioned synthesis processes. However, for economical ortechnical reasons, it may be more expedient to prepare some of thecompounds I from similar 2-phenylpyridines which differ in the meaningof one radical.

The compounds of the formula IIa

are novel.

In general, the 2-halopyridines II can be prepared, for example, bydiazotization of the corresponding 5-aminopyridines IX¹)

¹⁾ for their preparation, cf. J. Med. Chem 16, 319-327 (1973)—preferably using a nitrite such as tert-butylnitrite andisopentylnitrite—C followed by reaction of the diazonium salt withacetic anhydride analogously to Process C):

The process is preferably carried out in an anhydrous system, forexample in hydrogen chloride-containing glacial acetic acid, in dioxane,absolute ethanol, tetrahydrofuran, acetonitrile or in acetone. Thereaction temperature is usually from (−30) to 80° C.

In general, the components of the diazotization reaction are employed inapproximately stoichiometric amounts; however, it may also beadvantageous to use an excess of one of the components, for example withrespect to a conversion of the other component which is as complete aspossible. Preference is given to using an excess of nitrite, up to abouttwo times the molar amount, based on the amount of IX.

The acetic anhydride is advantageously employed in approximatelyequimolar amounts or in excess, based on the diazonium salt. In general,a large excess of acetic anhydride (up to about 100 times the molaramount), based on the amount of diazonium salt, has been found to beparticularly advantageous.

The 2-halopyridines II where R¹=C₁-C₆-alkylsulfinyl can subsequently beoxidized to the corresponding compounds II where R¹=C₁-C₆-alkylsulfonyl,as described under Process E) for the compounds I whereR¹=C₁-C₆-alkylsulfinyl.

Unless stated otherwise, all the processes described above areadvantageously carried out at atmospheric pressure or under theautogenous pressure of the reaction mixture in question.

The work-up of the reaction mixtures is usually carried out in aconventional manner, for example by dilution of the reaction solutionwith water and subsequent isolation of the product by filtration,crystallization or solvent extraction, or by removing the solvent,partitioning the residue in a mixture of water and a suitable organicsolvent and work-up of the organic phase to afford the product.

The substituted 2-phenylpyridines I can be obtained as isomer mixturesin the preparation; however, if desired, these can be separated intolargely pure isomers using customary methods such as crystallization orchromatography, including chromatography over an optically activeadsorbent. Pure optically active isomers can be prepared advantageouslyfrom suitable optically active starting materials.

Agriculturally useful salts of the compounds I can be formed by reactionwith a base of the corresponding cation, preferably an alkali metalhydroxide or hydride.

Salts of I where the metal ion is not an alkali metal ion can also beprepared by cation exchange of the corresponding alkali metal salt in aconventional manner, similarly ammonium, phosphonium, sulfonium andsulfoxonium salts by means of ammonia, phosphonium, sulfonium orsulfoxonium hydroxides.

The compounds I and their agriculturally useful salts are suitable, bothin the form of isomer mixtures and in the form of the pure isomers, foruse as herbicides. The herbicidal compositions comprising I controlvegetation on non-crop areas very efficiently, especially at high ratesof application. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method used in each case, the compounds I,or herbicidal compositions comprising them, can additionally be employedin a further number of crop plants for eliminating undesirable plants.Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica),Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which toleratethe action of herbicides owing to breeding, including geneticengineering methods. Moreover, the substituted 2-phenylpyridines I arealso suitable for the desiccation and/or defoliation of plants.

As desiccants, they are suitable, in particular, for desiccating theaerial parts of crop plants such as potatoes, oilseed rape, sunflowersand soybeans. This allows completely mechanical harvesting of theseimportant crop plants.

Also of economic interest is the facilitation of harvesting, which ismade possible by dehiscence, or reduction of the adherence to the tree,both concentrated over a period of time, in citrus fruit, olives orother species and varieties of pomaceous fruit, stone fruit and nuts.The same mechanism, ie. promotion of the formation of abscission tissuebetween fruit or leaf and shoot of the plants, is also important forreadily controllable defoliation of useful plants, in particular cotton.

Moreover, shortening the period within which the individual cottonplants mature results in improved fiber quality after harvesting.

The compounds I, or the compositions comprising them, can be used forexample in the form of ready-to-spray aqueous solutions, powders,suspensions, also highly-concentrated aqueous, oily or other suspensionsor dispersions, emulsions, oil dispersions, pastes, dusts, materials forspreading, or granules, by means of spraying, atomizing, dusting,spreading or pouring. The use forms depend on the intended aims; in anycase, they should guarantee a very fine distribution of the activecompounds according to the invention.

Suitable inert auxiliaries are essentially: mineral oil fractions ofmedium to high boiling point, such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstrates, either as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is possible to prepare concentratescomprising active compound, wetting agent, tackifier, dispersant oremulsifier and, if desired, solvent or oil, which are suitable fordilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, eg.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, andof fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene, or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active compounds together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight, of at least one active compound. Theactive compounds are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to the NMR spectrum).

The formulation examples which follow illustrate the preparation of suchproducts:

I. 20 parts by weight of the compound No. Ia.363 are dissolved in amixture composed of 80 parts by weight of alkylated benzene, 10 parts byweight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calciumdodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000parts by weight of water and finely distributing it therein gives anaqueous dispersion which comprises 0.02% by weight of the activecompound.

II. 20 parts by weight of the compound No. Ia.362 are dissolved in amixture composed of 40 parts by weight of cyclohexanone, 30 parts byweight of isobutanol, 20 parts by weight of the adduct of 7 mol ofethylene oxide to 1 mol of isooctyl-phenol and 10 parts by weight of theadduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active compound.

III. 20 parts by weight of the active compound No. Ia.374 are dissolvedin a mixture composed of 25 parts by weight of cyclohexanone, 65 partsby weight of a mineral oil fraction of boiling point 210 to 280° C. and10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol ofcastor oil. Pouring the solution into 100,000 parts by weight of waterand finely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. Ia.363 are mixedthoroughly with 3 parts by weight of sodiumdiisobutyl-naphthalene-a-sulfonate, 17 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activecompound.

V. 3 parts by weight of the active compound No. Ia.362 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active compound.

VI. 20 parts by weight of the active compound No. Ia.374 are mixedintimately with 2 parts by weight of calcium dodecyl benzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. Ia.363 is dissolved in amixture composed of 70 parts by weight of cyclohexanone, parts by weightof ethoxylated isooctylphenol and 10 parts by weight of ethoxylatedcastor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. Ia.374 is dissolved in amixture composed of 80 parts by weight of cyclohexanone and 20 parts byweight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylatedcastor oil; BASF AG). This gives a stable emulsion concentrate.

The active compounds I or the herbicidal compositions can be appliedpre- or post-emergence. If the active compounds are less well toleratedby certain crop plants, application techniques may be used in which theherbicidal compositions are sprayed, with the aid of the sprayingequipment, in such a way that they come into as little contact aspossible, if any, with the leaves of the sensitive crop plants, whilethe active compounds reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of active compound I are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, thesubstituted 2-phenylpyridines I may be mixed with a large number ofrepresentatives of other herbicidal or growth-regulating active compoundgroups and then applied concomitantly. Suitable components for mixturesare, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides,aminophosphoric acid and its derivatives, aminotriazoles, anilides,aryloxy/ hetaryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid andits derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitro-anilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyl-uracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetra-hydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonyl-ureas, triazines, triazinones, triazolinones,triazolecarbox-amides and uracils.

It may furthermore be advantageous to apply the compounds I, alone orelse concomitantly in combination with other herbicides, in the form ofa mixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

PREPARATION EXAMPLES Example 1 Compound Ia.363 in Table 1

8.5 ml of a 2 molar solution of isopropylmagnesium chloride intetrahydrofuran were added dropwise to a solution of 3.7 g of5-bromo-2-chloro-4-fluoroanisole in 80 ml of tetrahydrofuran. After 30minutes of stirring, the resulting mixture was, at 0° C., added dropwiseto a solution of 5.7 g of3-chloro-5-(methylsulfonyloxy)-2-(phenylsulfonyl)pyridine in 100 ml oftetrahydrofuran. The entire reaction mixture was then stirred atapproximately 20° C. for 17 h. The mixture was subsequently heated atreflux temperature for 72 hours. The low-boiling fractions were thendistilled off. The residue was taken up in 11 of ethyl acetate. Theorganic phase was washed with 2×250 ml of water, dried over magnesiumsulfate and finally concentrated. The crude product was purified bysilica gel chromatography (mobile phase: ethyl acetate/cyclohexane(1:1)). Yield: 2.9 g.

Intermediate 1.1: 3-Chloro-2-hydroxy-5-nitropyridine Initially, 190.9 gof 2-hydroxy-5-nitropyridine were dissolved at 50° C. in 650 ml of conc.hydrochloric acid. Over a period of one hour, a solution of 42.9 g ofpotassium chlorate in 600 ml of water was added dropwise to thismixture. After cooling to approximately 20° C., the mixture was stirredfor another 45 minutes and then cooled to 0° C. The solid fraction wassubsequently filtered off and suspended in 200 ml of water. Theundissolved product was finally filtered off and dried at 50° C. underreduced pressure. Yield: 162.9 g; m.p.: 197-198° C.

Intermediate 1.2: 2,3-Dichloro-5-nitropyridine

At 0° C., 39.9 g of quinoline and, after 5 minutes and a little at atime, 108 g of 3-chloro-2-hydroxy-5-nitropyridine were added to 95 g ofphosphorus oxytrichloride. After addition of a further 30 ml ofphosphorus oxytrichloride, the mixture was heated at reflux temperaturefor 2 hours. For work-up, the reaction mixture was cooled to 50-60° C.and stirred into approximately 3 1 of ice-water. The mixture wassubsequently stirred for another 2 hours, and the resulting solidfraction was then filtered off, washed with 500 ml of water and driedunder reduced pressure. Yield: 110.7 g.

Intermediate 1.3: 2,3-Dichloro-5-aminopyridine 1 g of platinum onactivated carbon was added to a solution of 67.4 g of2,3-dichloro-5-nitropyridine in 800 ml of tetrahydrofuran. 25 1 ofhydrogen were subsequently introduced, and the reaction mixture was,toward the end of the reaction, heated to 50° C. The insolublecomponents were then filtered off. The filtrate was concentrated. Yield:56 g.

Intermediate 1.4: 2,3-Dichloro-5-azidopyridine Tetrafluoroborate

At 0° C., a solution of 45.6 g of sodium nitrite in 100 ml of water wasadded dropwise to a solution of 98 g of 2,3-dichloro-5-aminopyridine in600 ml of 48% strength tetrafluoroboric acid. After one hour, theresulting solid was filtered off and, in order to prevent suddendecomposition, processed further in a moist state.

Intermediate 1.5: 5-Acetyloxy-2,3-dichloropyridine

42 g of the diazonium salt from intermediate 1.4 and 300 ml of aceticanhydride were heated at reflux temperature for one hour. The mixturewas subsequently concentrated. The residue was taken up in 400 ml ofdiethyl ether, and the solution was washed twice with in each case 200ml of water, dried over magnesium sulfate and finally reconcentrated.The crude product was purified by silica gel chromatography (mobilephase: ethyl acetate/cyclohexane (1:1)). Yield: 16 g.

Intermediate 1.6: 2,3-Dichloro-5-hydroxypyridine

At 0° C., a solution of 13 g of sodium hydroxide in 80 ml of water wasadded to 16 g of 5-acetyloxy-2,3-dichloropyridine in 100 ml ofice-water. The mixture was subsequently initially stirred at 0° C. forone hour and then at approximately 20° C. for 17 hours, and the reactionmixture was then washed with 150 ml of ethyl acetate. The mixture wasacidified up to a pH of 4-5 by addition of acetic acid and thenextracted three times with 100 ml of ethyl acetate each time. Thecombined organic phases were dried over magnesium sulfate and finallyconcentrated. Yield: 12.2 g.

Intermediate 1.7: 2,3-Dichloro-5-(methylsulfonyloxy)pyridine

At 0° C., initially 7.9 g of triethylamine and then 8.5 g ofmethanesulfonyl chloride were added to 11.6 g of2,3-dichloro-5-hydroxypyridine in 150 ml of methylene chloride. Themixture was subsequently stirred at approximately 20° C. for 17 hoursand then washed with 100 ml of water. The organic phase was dried overmagnesium sulfate and then concentrated. The resulting crude product waspurified by silica gel chromatography (mobile phase: ethylacetate/cyclohexane (1:1)). Yield: 9.1 g.

Intermediate 1.8:2-Chloro-5-(methylsulfonyloxy)-2-(phenylsulfonyl)pyridine

A mixture of 8.9 g of 2,3-dichloro-5-(methylsulfonyloxy)pyridine, 4.2 gof thiophenol and 20 mg of copper powder was heated at 170° C. for 2hours and, after cooling to approximately 20° C., admixed dropwise firstwith a mixture of 50 ml of glacial acetic acid and 20 ml of water andthen, with cooling, with a mixture of 157 g of aqueous sodiumhypochlorite solution (containing 13% of active chlorine) and 50 ml ofwater. The mixture was subsequently stirred at approximately 20° C. for17 hours, and the entire reaction mixture was then stirred into 300 mlof water. The mixture was extracted three times with 200 ml of ethylacetate each time, and the combined organic phases were then dried overmagnesium sulfate and finally concentrated. The crude product waspurified by silica gel chromatography (mobile phase: ethylacetate/cyclohexane (1:1)). Yield: 5.7 g.

Example 2 Compound Ia.363 in Table 1

Initially, a solution of 13.5 g of sodium bicarbonate in 100 ml of waterwas added dropwise to a mixture of2,3-dichloro-5-methylsulfonylpyridine,4-chloro-2-fluoro-5-methoxyboronic acid and 100 ml of tetrahydrofuran,and 1 g of tetrakis(triphenylphosphine)palladium was then added. Themixture was stirred at reflux temperature for 14 hours, after which 150ml of methyl tert-butyl ether were added to the reaction mixture. Theorganic phase was subsequently separated off. The aqueous phase wasextracted twice with in each case 150 ml of methyl tert-butyl ether. Thecombined organic phases were then dried over magnesium sulfate andfinally concentrated. The crude product was purified by silica gelchromatography (mobile phase: ethyl acetate/cyclohexane (1:1)). Yield:5.0 g.

Example 3 Compound Ia.362 in Table 1

14.4 ml of a 1 molar solution of boron tribromide in methylene chloridewere added dropwise to 4.8 g of2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-chloro-5-(methylsulfonyl-oxy)pyridine(compound No. Ia.363) in 100 ml of methylene chloride. The mixture wassubsequently stirred at approximately 20° C. for 37 hours and then atreflux temperature for 7 hours. 100 ml of ice-water were then addeddropwise to the reaction mixture. The phases were separated and theaqueous phase was then extracted twice with in each case 100 ml ofmethylene chloride. The combined organic phases were finally dried overmagnesium sulfate and then concentrated. The crude product was purifiedby silica gel chromatography (mobile phase: ethyl acetate/cyclohexane(1:1)). Yield 3.2 g.

Example 4 Compound Ia.374 in Table 1

0.3 g of potassium carbonate and 0.25 g of allyl bromide were addedsuccessively to 0.6 g of2-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-chloro-5-(methylsulfonyl-oxy)pyridine (compound No. Ia.362) in 100 ml of dimethylformamide. Thereaction mixture was subsequently stirred at approximately 20° C. for 17hours and then introduced into 300 ml of water. The resulting product ofvalue was extracted with 3 x 150 ml of methyl tert-butyl ether. Thecombined organic phases were dried over magnesium sulfate and finallyconcentrated. The crude product was purified by silica gelchromatography (mobile phase: ethyl acetate/cyclohexane (1:1)). Yield:80 mg.

The physical data of the active compounds I described above and of othercompounds according to the invention which were prepared in a similarmanner are listed in Table 2 below:

TABLE 2 No. R⁵ m.p. [° C.] Ia.159 OCH₂—CO—OCH₃ oil Ia.169OCH(CH₃)—CO—OCH₃(racemate & R oil enantiomer) Ia.362 OH 132-133 Ia.363OCH₃ 118-120 Ia.374 OCH₂—CH═CH₂ oil Ia.381 OCH₂—C≡CH 110-112 Ia.636OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ oil (R enantiomer) Ia.637OCH(CH₃)—CO—OCH₂—CH═CH₂ oil (R enantiomer)

Use Examples (Herbicidal Activity)

The herbicidal activity of the substituted 2-phenylpyridines I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this has been adverselyaffected by the active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active compounds which had been suspended or emulsifiedin water. For this purpose, the test plants were either sown directlyand grown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment. The rate of application for the post-emergence treatment was15.6 and 7.8 g of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

Scientific name Common name Abutilon theophrasti velvet leaf Amaranthusretrofiexus redroot pigweed Chenopodium album lambsquarters (goosefoot)Ipornoea species morning glory Polygonum persicaria redshank

At application rates of 15.6 and 7.8 g of a.s./ha, the compounds Nos.Ia.169, Ia.381 and Ia.636 (R enantiomer) displayed very good herbicidalactivity against the abovementioned plants.

Use Examples (Desiccant/defoliant Activity)

The test plants used were young cotton plants with four leaves (withoutcotyledons) which had been grown under greenhouse conditions (relativeatmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The young cotton plants were subjected to foliar treatment to a runoffpoint with aqueous preparations of the active compounds (with anaddition of 0.15% by weight of the fatty alcohol alkoxide Plurafac® LF700 2), based on the spray mixture). The amount of water applied was1000 l/ha (converted). After 13 days, the number of leaves shed and thedegree of defoliation in % were determined.

No leaves were shed in the untreated control plants.

We claim:
 1. A compound of formula I

where: n is zero or 1; R¹ is aminosulfonyl, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl; R²,R³ independently ofone another are hydrogen or halogen; R⁴ is cyano, hydroxyl, halogen,C₁-C₆-alkoxy or phenylmethoxy, where the phenyl ring is unsubstituted orcarries from one to three substituents, in each case selected from thegroup consisting of hydroxyl, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, hydroxycarbonyl, (C₁-C₆-alkoxy)carbonyland (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkoxy; R⁵ is hydrogen, nitro, cyano,hydroxylamino, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —COCl, —CO—OR⁶,—CO—N(R⁷)R⁸, —CO—(C₁-C₄-alkylene)—CO—OR⁶,—CO—O—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸, —X¹—(C₁-C₄-alkylene)—CO—R⁶,—X¹—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶,—X¹—(C₁-C₄-alkylene)—CO—N(R⁷)R⁸, —X¹—R⁹, —CH═C(R¹⁰)—CO—OR⁶,—CH═C(R¹⁰)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CH═C(R¹⁰)—CO—N(R⁷)R⁸, formyl,—CO—R⁶,

 —C(R⁸)═N—OR¹⁵, —X¹—(C₁C₄-alkylene)—C(R⁸)═N—OR¹⁵,—CH═C(R¹⁰)—C(R⁸)═N—OR¹⁵, —CH(C₁-C₆-alkoxy)₂, —CN(R¹⁶)R¹⁷,—N(R¹⁶)—SO₂—(C₁-C₆-alkyl), —CN(R¹⁶)—CO—(C₁-C₆-alkyl), chlorosulfonyl,hydroxysulfonyl or —SO₂—N(R¹⁸)R¹⁹; R⁶ is hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl orC₁-C₆-alkoxy-C₁-C₆-alkyl; R⁷ is hydrogen or C₁-C₆-alkyl; R⁸ is hydrogen,hydroxyl, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,phenyl-C₁-C₆-alkoxy, C₃-C₆-alkenyloxy or C₃-C₆-alkynyloxy; R⁹ ishydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,C₃-C₆-cycloalkyl or C₁-C₆-alkoxy-C₁-C₆-alkyl; R¹⁰ is hydrogen, halogenor C₁ ₆-alkyl; R¹¹-R¹⁴ independently of one another are hydrogen,C₁-C₆-alkyl or (C₁-C₆-alkoxy)carbonyl; R¹⁵ is hydrogen, C₁-C₆-alkyl,phenyl-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, C₃-C₆-alkenyl orC₃-C₆-alkynyl; R¹⁶ is hydrogen or C₁-C₆-alkyl; R¹⁷ is hydrogen,C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy; R¹⁸ is hydrogen orC₁-C₆-alkyl; R¹⁹ is hydrogen, C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₆-alkyl,(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkoxy; X¹-X³ independentlyof one another are oxygen or sulfur; or an agriculturally useful salt ofthe compound wherein R⁶═hydrogen.
 2. The compound of formula I definedin claim 1 or the salt thereof, where R⁵ is hydrogen, nitro, cyano,hydroxylamino, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —COCl, —CO—OR⁶,—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —CO—(C₁-C₄-alkylene)—CO—OR⁶,—CO—(C₁-C₄-alkylene)—CO—O—(C₁-C₄-alkylene)—CO—OR⁶, —COR⁹, formyl,—CH═N—OR¹⁵ or —CNH₂; R⁶ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl or C₁-C₆-alkoxy-C₁-C₆-alkyl; R⁹ is hydrogen, C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-alkynyl and R¹⁵ is C₁-C₆-alkyl.
 3. A herbicidalcomposition, comprising an effective amount of at least one compound offormula I defined in claim 1 or the salt thereof, and at least one inertliquid or solid carrier and optionally at least one surfactant.
 4. Acomposition for desiccating or defoliating plants, comprising aneffective amount of at least one compound of formula I defined in claim1 or the salt thereof, and at least one inert liquid or solid carrierand optionally at least one surfactant.
 5. A process of preparing thecomposition defined in claim 3, which comprises mixing the effectiveamount of the at least one compound of formula I or the salt thereof, atleast one inert liquid or solid carrier and optionally at least onesurfactant.
 6. A process of preparing the composition defined in claim4, which comprises mixing the effective amount of the at least onecompound of formula I or the salt thereof, at least one inert liquid orsolid carrier and optionally at least one surfactant.
 7. A method forcontrolling undesirable vegetation, which comprises allowing aneffective amount of at least one compound of formula I defined in claim1 or the salt thereof, to act on plants, their habitat or on seeds.
 8. Amethod for desiccating or defoliating plants, which comprises allowingan effective amount of at least one compound of formula I defined inclaim 1 or the salt thereof, to act on plants.
 9. The process of claim8, wherein the plants are cotton plants.
 10. A compound of formula IIa

where Hal is chlorine or bromine, and R¹ is aminosulfonyl,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl.